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1.
Medicine (Baltimore) ; 98(36): e17009, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31490383

RESUMO

Erythrina corallodendron L., a kind of landscape tree, has long been used as a traditional medicine. In this study, the composition of essential oil extracted from the leaves was analysed by GC-MS (gas chromatograph-mass spectrometer), with linalool identified as the main compound. Its cytotoxicity against MDA-MB-231, MCF-7 and HMLE cells was examined by MTT and cloning assays. Transwell and wound-healing assays were used to examine the inhibition of migration and invasion. Western blot, qRT-PCR and immunofluorescence staining were used to measure the mRNA and protein expression of factors related to EMT (snail, slug, E-cadherin, N-cadherin and vimentin). The essential oil of Erythrina corallodendron leaves was found to inhibit the proliferation, migration and invasion of breast cancer cells in a dose-dependent manner. The findings of this study suggest that the essential oil of E. corallodendron leaves may merit further investigation as a potential clinical or adjuvant drug for treating breast cancer migration and invasion.


Assuntos
Adenocarcinoma/tratamento farmacológico , Antineoplásicos Fitogênicos/análise , Neoplasias da Mama/tratamento farmacológico , Erythrina/química , Óleos Voláteis/uso terapêutico , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Transição Epitelial-Mesenquimal/efeitos dos fármacos , Humanos , Células MCF-7 , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Fitoterapia , Folhas de Planta/química
2.
J Pharm Pharmacol ; 71(6): 1007-1016, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30793315

RESUMO

OBJECTIVES: Recent studies showed that distinct extracts of Erythrina species used in the traditional medicine of sub-Saharan Africa are protective against stress conditions. However, the underlying molecular mechanisms as well as relevant compounds remain unclear. METHODS: We used the model organism Caenorhabditis elegans to investigate compounds isolated from the stem bark of Erythrina melanacantha (abyssinone V (1), abyssinon-4'O-methylether (2), sigmoidin B-4'O-methylether (3), glabranin (4), 8-prenylnaringenin (5), citflavanone (6), exiguaflavanone (7) and homoeriodictyol (8)). Antioxidative capacity in vitro (trolox equivalent antioxidative capacity assay) and modulation of oxidative stress in vivo (2', 7'-dichlorofluorescein assay) were investigated; stress resistance was analysed using the nucleic acid stain SYTOX green. KEY FINDINGS: None of the prenylated flavonoids caused protection against thermal stress; in contrast, most of the compounds (1, 4, 5, 8) decreased stress resistance. None of the compounds decreased the accumulation of reactive oxygen species, but abyssinone V (1) caused an increase in oxidative stress. In line with these results, none of these compounds showed radical-scavenging effects in vitro. CONCLUSIONS: The stem bark of E. melanacantha contains various prenylated flavonoids, but no compound protected C. elegans against stress conditions. In contrast, abyssinone V increases oxidative stress and reduces stress resistance in this model organism.


Assuntos
Erythrina/química , Flavonoides/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , África ao Sul do Saara , Animais , Antioxidantes/metabolismo , Caenorhabditis elegans/efeitos dos fármacos , Flavonoides/isolamento & purificação , Medicina Tradicional Africana/métodos , Casca de Planta , Extratos Vegetais/química , Espécies Reativas de Oxigênio/metabolismo
3.
Phytother Res ; 33(5): 1258-1276, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30767297

RESUMO

Erythrina L. genus (Fabaceae) comprises about 115 species, and it has been extensively studied, mainly because of its alkaloids, which have pharmacological properties. References demonstrated that Erythrina spp. have a potential to act in the central nervous system, presenting anxiolytic and anticonvulsant properties already established. Phytochemical investigations confirmed the presence of tetracyclic alkaloids as the major compounds. However, other alkaloid classes have also been reported, including dimeric and trimeric substances, coupled through direct polymerization or two erythrinine units via an acetyl glucose. The present review covers the relevant literature from 1990 until 2017 and outlines the current data on chemical composition and preclinical and clinical studies on Erythrina species. Additionally, the quite striking analogy in the biosynthetic route of erythrin, morphinans, and Amaryllidaceae family alkaloids was also discussed.


Assuntos
Alcaloides/uso terapêutico , Erythrina/química , Extratos Vegetais/química , Alcaloides/farmacologia , Humanos
4.
Phytomedicine ; 53: 9-17, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30668417

RESUMO

BACKGROUND: Natural antioxidants and anti-inflammatory agents have the ability to restore normal balance to destructed liver cells. The genus Erythrina has attracted attention for its broad spectrum of physiological activities and its rich polyphenolic and alkaloid contents. HYPOTHESIS/PURPOSE: The major phytoconstituents of Erythrina × neillii, an ornamental coral tree and a hybrid between E. herbacea and E. humeana that was not previously studied, were investigated. The hepatoprotective effect and underlying mechanisms were also assessed. STUDY DESIGN AND METHODS: The main phytoconstituents in the different fractions of the alcoholic leaf extract (dichloromethane and ethyl acetate) were identified using high resolution high-performance liquid chromatography coupled with mass spectrometry (HR-HPLC-MS-MS) based on the fragmentation pattern and molecular formula of the identified compounds and on previous literature. In addition, the hepatoprotective, anti-inflammatory and antioxidant activities of three doses of E. × neillii alcoholic leaf extract (100, 250, 500 mg/kg) were investigated in methotrexate (MTX)-intoxicated rats and were compared with those of silymarin-treated rats. Liver function parameters were obtained, and a histopathological study was performed. In addition, the anti-inflammatory mediators and the antioxidant system in the liver tissues were assessed. RESULTS: The dichloromethane extract revealed an abundance of alkaloids (25), in addition to tentatively identifying flavone (1), flavanone (1) and three fatty acids. Additionally, thirty-six compounds belonging to different classes of phytoconstituents with a predominance of flavonoids (21), O/C-flavone and flavonol glycosides, followed by alkaloids (9), fatty acids (4) and (2), and phenolic glycoside were identified in the ethyl acetate extract. Compared with MTX, alcoholic leaf extract (500 mg/kg) ameliorated the MTX-induced alterations by improving several biochemical marker levels, fighting oxidative stress in serum and liver tissues, and decreasing inflammatory mediators; this finding was further confirmed by the histopathological study. CONCLUSION: This study reveals E. × neillii, a rich source of flavonoids and alkaloids, which could be further exploited to provide a promising and safe antihepatotoxic agent source.


Assuntos
Erythrina/química , Fígado/efeitos dos fármacos , Extratos Vegetais/farmacologia , Substâncias Protetoras/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antioxidantes/química , Antioxidantes/metabolismo , Antioxidantes/farmacologia , Doença Hepática Induzida por Substâncias e Drogas/etiologia , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Cromatografia Líquida de Alta Pressão , Flavonoides/análise , Flavonoides/química , Glicosídeos/análise , Glicosídeos/química , Fígado/metabolismo , Fígado/patologia , Masculino , Metotrexato/toxicidade , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/química , Folhas de Planta/química , Substâncias Protetoras/química , Ratos Wistar , Espectrometria de Massas em Tandem
5.
Pest Manag Sci ; 74(1): 210-218, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-28799721

RESUMO

BACKGROUND: The cotton aphid (Aphis gossypii Glover) is one of the most invasive pests of cotton. Many botanical phytochemicals have a long history as a source of insecticides, and as templates for new insecticides. This study was undertaken to isolate aphicidal compounds from the seeds of Erythrina crista-galli L. using the bioassay-guided isolation method. RESULTS: Three novel and 11 known Erythrina alkaloids were isolated. Erysodine (9), erysovine (10), erysotrine (8) and erythraline (11) showed moderate to excellent aphicidal activity with LD50 values of 7.48, 6.68, 5.13 and 4.67 ng aphid-1 , respectively. The Potter spray tower bioassay gave corresponding LC50 values of 186.81, 165.35, 163.74 and 112.78 µg ml-1 . A unique substructure, which presents an sp3 methylene at C-8, a non-oxygenated site at N-9 and a conjugated dienes group (Δ1,2 and Δ6,7 ), plays a crucial role in the aphicidal activity. Application of erythraline (11) led to different increases in the activities of superoxide dismutase, catalase and glutathione S-transferase. CONCLUSION: The study demonstrated that the Erythrina alkaloids erysodine (9), erysovine (10), erysotrine (8) and erythraline (11) have potential use as botanical aphicides for commercial application, or as templates for the development of new insecticides. © 2017 Society of Chemical Industry.


Assuntos
Alcaloides , Afídeos , Erythrina/química , Controle de Insetos , Inseticidas , Animais , Dose Letal Mediana , Sementes/química
6.
J Nat Med ; 72(1): 260-266, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29151157

RESUMO

Erypoegin K is an isoflavone isolated from the stem bark of Erythrina poeppigiana. It contains a furan group at the A-ring of the core isoflavone structure and can inhibit the activity of glyoxalase I, an enzyme that catalyzes the detoxification of methylglyoxal (MG), a by-product of glycolysis. In the present study, we found that erypoegin K has a potent cytotoxic effect on human leukemia HL-60 cells. Its cytotoxic effect was much stronger than that of a known glyoxalase I inhibitor S-p-bromobenzylglutathione cyclopentyl diester. Conversely, erypoegin K demonstrated weak cytotoxicity toward normal human peripheral lymphocytes. The treatment of HL-60 cells with erypoegin K significantly induced caspase-3 activity, whereas the pretreatment of the cells with caspase-3 inhibitor suppressed erypoegin K-induced cell death. Furthermore, nuclear condensation and apoptotic genome DNA fragmentation were observed in erypoegin K-treated HL-60 cells. These results indicated that the observed cell death was mediated by apoptosis. In addition, the toxic compound MG was highly accumulated in the culture medium of erypoegin K-treated HL-60 cells, suggesting that cell apoptosis was triggered by extracellular MG. The present study showed that erypoegin K has a potent apoptosis-inducing effect on cancerous cell lines, such as HL-60.


Assuntos
Benzofuranos/química , Erythrina/química , Células HL-60/química , Isoflavonas/química , Leucemia/tratamento farmacológico , Apoptose , Humanos , Leucemia/patologia
7.
Biomed Pharmacother ; 96: 1230-1239, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29174035

RESUMO

The objective of this study was to verify a possible neuroprotective effect of the ethanolic extract of Erythrina velutina (EEEV). Male Swiss mice were submitted to transient cerebral ischemia by occlusion of both carotid arteries for 30 min and treated for 5 days with EEEV (200 or 400 mg/kg) or Memantine (MEM) 10 mg/kg, with initiation of treatment 2 or 24 h after Ischemia. On the 6th day after the induction of ischemia, the animals were submitted to evaluation of locomotor activity and memory and then sacrificed. The brains were dissected for the removal of the prefrontal cortex (PFC), hippocampus (HC) and striatum (ST) for determination of amino acid concentrations. In the step down and Y-maze tests, ischemia caused damage to the animals and treatment with EEEV or MEM reversed this effect. The animals submitted to ischemia also showed memory deficit in the object recognition test, an effect that was reverted by EEEV400 and MEM10. Amino acid dosage showed an increase in excitatory amino acid concentrations in the PFC of the ischemic animals and this effect was reversed by the treatment with EEEV400/24H. Regarding the inhibitory amino acids, ischemia caused an increase of taurine in the PFC while treatment with MEM10/24H or EEEV400/24H reversed this effect. In HC, an increase in excitatory amino acids was also observed in ischemiated animals having treatment with EEEV200/2H or EEEV400/24H reversed this effect. Similar effect was also observed in the same area in relation to the inhibitory amino acids with treatment with MEM10/24H or EEEV400/24H. In the ST, ischemia was also able to cause an increase in excitatory amino acids that was reversed more efficiently by the treatments with MEM10/24H and EEEV200. Also in this area, an increase of taurine and GABA was observed and only the treatment with EEEV200/2H showed a reversion of this effect. In view of these findings, EEEV presents a neuroprotective effect possibly due to its action on amino acid concentrations, and is therefore a potential therapeutic tool in reducing the damage caused by ischemia.


Assuntos
Isquemia Encefálica/tratamento farmacológico , Erythrina/química , Extratos Vegetais/farmacologia , Aminoácidos/metabolismo , Animais , Encéfalo/efeitos dos fármacos , Isquemia Encefálica/metabolismo , Infarto Cerebral/tratamento farmacológico , Infarto Cerebral/metabolismo , Etanol/química , Masculino , Memória/efeitos dos fármacos , Camundongos , Fármacos Neuroprotetores/farmacologia
8.
Phytochemistry ; 141: 140-146, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28614730

RESUMO

A series of prenylated flavonoids was obtained from antigenotoxic extracts and fractions of stem bark of Erythrina latissima E. Mey (Leguminosae). In addition to five constituents never reported before, i.e. (2S)-5,7-dihydroxy-2-(4-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)chroman-4-one (erylatissin D), (2S)-5,7-dihydroxy-2-(4-methoxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)chroman-4-one (erylatissin E), 5,7-dihydroxy-3-(4-methoxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)-4H-chromen-4-one (erylatissin F), (2S)-5,7,8'-trihydroxy-2',2'-dimethyl-[2,6'-bichroman]-4-one (erylatissin G) and (2S)-5,7-dihydroxy-8'-methoxy-2',2'-dimethyl-[2,6'-bichroman]-4-one (dihydroabyssinin I), 18 known flavonoids were identified. Evaluation of the antigenotoxic properties (against genotoxicity induced by aflatoxin B1, metabolically activated) in the Vitotox assay revealed that most flavonoids were active. Sigmoidin A and B showed the highest activity, with an IC50 value of 18.7 µg/mL, equivalent to that of curcumin (IC50 18.4 µg/mL), used as a reference antigenotoxic compound.


Assuntos
Antimutagênicos/química , Erythrina/química , Flavonoides/química , Casca de Planta/química , Aflatoxina B1 , Antimutagênicos/isolamento & purificação , Flavonoides/isolamento & purificação , Estrutura Molecular , Testes de Mutagenicidade , Prenilação
9.
J Mass Spectrom ; 52(9): 571-579, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28644563

RESUMO

Alkaloids from plants of the genus Erythrina display important biological activities, including anxiolytic action. Characterization of these alkaloids by mass spectrometry (MS) has contributed to the construction of a spectral library, has improved understanding of their structures and has supported the proposal of fragmentation mechanisms in light of density functional calculations. In this study, we have used low-resolution and high-resolution MSn analyses to investigate the fragmentation patterns of erythrinian alkaloids; we have employed the B3LYP/6-31+G(d,p) model to obtain their reactive sites. To suggest the fragmentation mechanism of these alkaloids, we have studied their protonation sites by density functional calculation, and we have obtained their molecular electrostatic potential map and their gas-phase basicity values. These analyses have indicated the most basic sites on the basis of the proton affinities of the nitrogen and oxygen atoms. The protonated molecules were generated by two major fragmentations, namely, neutral loss of CH3 OH followed by elimination of H2 O. High-resolution analysis confirmed elimination of NH3 by comparison with the losses of H2 and •CH3 . NH3 was eliminated from compounds that did not bear a substituent on ring C. The benzylic carbocation initiated the dissociation mechanism, and the first reaction involved charge transfer from a lone pair of electrons in the oxygen atoms. The second reaction consisted of ring contraction with loss of a CO molecule. The presence of hydroxy and epoxy groups could change the intensity or the occurrence of the fragmentation pathways. Given that erythrinian alkaloids are applied in therapeutics and are promising leads for the development of new drugs, the present results could aid identification of several analogues of these alkaloids in biological samples and advance pharmacokinetic studies of new plant derivatives based on MSn and MS/MS analyses. Copyright © 2017 John Wiley & Sons, Ltd.


Assuntos
Alcaloides/análise , Erythrina/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Alcaloides/química , Aminas/química , Sítios de Ligação , Monóxido de Carbono/química , Hidrogênio/química , Modelos Químicos , Nitrogênio/química , Extratos Vegetais/análise , Extratos Vegetais/química , Prótons , Eletricidade Estática , Espectrometria de Massas em Tandem/métodos
10.
Biochem Cell Biol ; 95(2): 243-250, 2017 04.
Artigo em Inglês | MEDLINE | ID: mdl-28177773

RESUMO

Trypsin and chymotrypsin inhibitors from Erythrina velutina seeds have been previously isolated by our group. In previous studies using a sepsis model, we demonstrated the antitumor and anti-inflammatory action of these compounds. This study aimed to evaluate the gastroprotective and antielastase effects of protein inhibitors from E. velutina seeds in an experimental stress-induced ulcer model. Two protein isolates from E. velutina seeds, with antitrypsin (PIAT) and antichymotrypsin (PIAQ) activities, were tested. Both protein isolates showed a high affinity and inhibitory effect against human neutrophil elastase, with 84% and 85% inhibition, respectively. Gastric ulcer was induced using ethanol (99%) in 6 groups of animals (female Wistar rats, n = 6). Before ulcer induction, these animals were treated for 5 days with one of the following: (1) PIAT (0.2 mg·kg-1), (2) PIAT (0.4 mg·kg-1), (3) PIAQ (0.035 mg·kg-1), (4) ranitidine hydrochloride (50 mg·kg-1), (5) saline solution (0.9%), or (6) no intervention (sham). Both PIAT and PIAQ protected gastric mucosa, preventing hemorrhagic lesions, edema, and mucus loss. No histologic toxic effects of PIAT or PIAQ were seen in liver and pancreatic cells. Our results show that protein isolates from E. velutina seeds have potential gastroprotective effects, placing these compounds as natural candidates for gastric ulcer prevention.


Assuntos
Anti-Inflamatórios/farmacologia , Inibidores Enzimáticos/farmacologia , Erythrina/química , Fármacos Gastrointestinais/farmacologia , Fitoterapia , Úlcera Gástrica/prevenção & controle , Animais , Anti-Inflamatórios/isolamento & purificação , Modelos Animais de Doenças , Inibidores Enzimáticos/isolamento & purificação , Etanol , Feminino , Mucosa Gástrica/efeitos dos fármacos , Mucosa Gástrica/enzimologia , Mucosa Gástrica/patologia , Fármacos Gastrointestinais/isolamento & purificação , Humanos , Elastase de Leucócito/antagonistas & inibidores , Elastase de Leucócito/metabolismo , Extratos Vegetais/química , Ranitidina/farmacologia , Ratos , Ratos Wistar , Sementes/química , Úlcera Gástrica/induzido quimicamente , Úlcera Gástrica/enzimologia , Úlcera Gástrica/patologia
11.
Nat Prod Commun ; 11(6): 781-6, 2016 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-27534115

RESUMO

Erythrina edulis Triana ex Micheli is a protein-enriched legume traditionally used for both dietary and medicinal purposes. In this paper, protein concentrate was obtained from the seed flour. SDS-PAGE analysis revealed a high number and intensity of bands in the range between 10 and 90 kDa. Neutrase, Flavourzyme, and Alcalase were used to hydrolyze the protein concentrate at different times. By SDS-PAGE, the lower resistance of proteins to Alcalase action was observed, providing hydrolyzates with higher radical scavenging activity. The 120 min-hydrolyzate showed ORAC and TEAC values of 2.51 and 0.91 µmol Trolox equivalents/mg of protein, respectively. A fraction lower than 3 kDa and rich in hydrophobic and aromatic amino acids was demonstrated to be mainly responsible for the observed activity. E. edulis could be a new alternative in the formulation of functional foods not only for its high protein content but also for the potential biological properties of its hydrolyzates.


Assuntos
Antioxidantes/química , Erythrina/química , Peptídeos/química , Proteínas de Plantas/química , Sementes/química , Cinética
12.
J Acupunct Meridian Stud ; 9(4): 207-12, 2016 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-27555226

RESUMO

Natural products derived from plant sources have been utilized to treat patients with numerous diseases. The phytochemical constituents present in ethanolic leaf extract of Erythrina variegata (ELEV) were identified by using high-performance liquid chromatography (HPLC) and gas chromatography-mass spectroscopy (GC-MS) analyses. Shade dried leaves were powdered and extracted with ethanol for analyses through HPLC to identify selected flavonoids and through GC-MS to identify other molecules. The HPLC analysis of ELEV showed the presence of gallic and caffeic acids as the major components at concentrations of 2.0 ppm and 0.1 ppm, respectively, as well as other components. GC-MS analysis revealed the presence of 3-eicosyne; 3,7,11,15-tetramethyl-2-hexadecen-1-ol; butanoic acid, 3-methyl-3,7-dimethyl-6-octenyl ester; phytol; 1,2-benzenedicarboxylic acid, diundecyl ester; 1-octanol, 2-butyl-; squalene; and 2H-pyran, 2-(7-heptadecynyloxy) tetrahydro-derivative. Because pharmacopuncture is a new evolving natural mode that uses herbal extracts for treating patients with various ailments with minimum pain and maximum effect, the results of this study are particularly important and show that ELEV possesses a wide range of phytochemical constituents, as indicated above, as effective active principle molecules that can be used individually or in combination to treat patients with various diseases.


Assuntos
Erythrina/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão , Cromatografia Gasosa-Espectrometria de Massas , Folhas de Planta/química
13.
Molecules ; 21(6)2016 Jun 03.
Artigo em Inglês | MEDLINE | ID: mdl-27271580

RESUMO

OBJECTIVES: The current study aimed at exploring the secondary metabolites content of Erythrina crista-galli aqueous methanol extract and assessing its phytoestrogenic and cytoprotective activities. METHODS: Isolation of the compounds was carried out using conventional chromatographic techniques. The structures of the isolated compounds were elucidated based on the UV, NMR spectral data along with their mass-spectrometric analyses. The phytoestrogenic activity was evaluated in-silico and in vitro using the Arabidopsis thaliana pER8: GUS reporter assay and the proliferation-enhancing activity of MCF-7 cells. KEY FINDINGS: Phytochemical investigation of E. crista-galli aqueous methanol extract resulted in the isolation and identification of five flavonoids. The plant extract and its fractions showed significant estrogenic activities compared to controls. CONCLUSION: Five flavonoids were identified from E. crista-galli aqueous methanol extract. To the best of our knowledge, among these flavonoids, apigenin-7-O-rhamnosyl-6-C-glucoside was isolated for the first time from nature. Moreover, luteolin-6-C-glucoside was isolated for the first time from this plant. The plant revealed promising phytoestrogenic activities. This gives rationale to some of its pharmacological properties and suggests additional phytoestrogenic effects, which have not been reported yet.


Assuntos
Erythrina/química , Fitoestrógenos/química , Extratos Vegetais/química , Polifenóis/química , Proliferação de Células/efeitos dos fármacos , Humanos , Células MCF-7 , Espectroscopia de Ressonância Magnética , Simulação de Acoplamento Molecular , Estrutura Molecular , Fitoestrógenos/administração & dosagem , Extratos Vegetais/administração & dosagem , Polifenóis/administração & dosagem
14.
Chemistry ; 22(21): 7262-7, 2016 05 17.
Artigo em Inglês | MEDLINE | ID: mdl-27076115

RESUMO

A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine.


Assuntos
Alcaloides/síntese química , Alcaloides de Amaryllidaceae/síntese química , Erythrina/química , Indóis/química , Fenantridinas/síntese química , Alcaloides/química , Alcaloides de Amaryllidaceae/química , Ciclização , Química Verde/métodos , Hidrocarbonetos Iodados/síntese química , Hidrocarbonetos Iodados/química , Indóis/síntese química , Oxirredução , Fenantridinas/química , Estereoisomerismo , Temperatura Ambiente
15.
J Ethnopharmacol ; 185: 171-81, 2016 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-26969405

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The bark of Erythrina stricta Roxb. (Fabaceae) has been used in Indian indigenous systems as a remedy for rheumatism, stomach-ache, asthma, dysentery, contact dermatitis, eczema and skin infections. However, there have been limited phytochemical or biological studies on the bark of E. stricta and there are no studies that align with its traditional medicinal uses. AIM OF THE STUDY: The aim of this study was to assess the antimicrobial and antioxidant activity of the stem bark of E. stricta to support its topical use in the treatment of contact dermatitis, eczema and skin infections and to isolate and identify any bioactive compounds. MATERIALS AND METHODS: MTT microdilution and disc diffusion assays were used to determine the antimicrobial activities of n-hexane, dichloromethane, ethyl acetate, methanol and water extracts of the bark of E. stricta. Column and preparative thin layer chromatography were used for the purification of the dichloromethane extract. The structures of the compounds isolated were elucidated by extensive 1D and 2D NMR spectroscopic techniques and comparison with published data. The antioxidant activities of the extracts were determined by DPPH free radical scavenging and FRAP assays and the antioxidant activity of the pure compounds by dot-blot and DPPH staining methods. RESULTS: The dichloromethane, ethyl acetate, and n-hexane extracts showed the most significant activity with MIC values of 7.8µg/mL, 125µg/mL, and 125µg/mL against a sensitive strain of Staphylococcus aureus. The dichloromethane and ethyl acetate extracts also showed significant activity against Candida albicans with MIC values of 125µg/mL and 1mg/mL respectively. GC-MS analysis of the n-hexane extract showed the presence of the antibacterial and antifungal compounds ß-caryophyllene, caryophyllene oxide, α-selinene, ß-selinene, selin-11-en-4-α-ol, α-copaene and δ-cadenine. Phytochemical studies of the dichloromethane extract led to the isolation of the novel compound erynone (1), together with six known compounds; wighteone (2), alpinum isoflavone (3), luteone (4), obovatin (5), erythrinassinate B (6) and isovanillin (7). Luteone (4) exhibited the most significant antibacterial activity with minimum inhibitory quantity (MIQ) values of 1.88µg, 1.88µg and 3.75µg, respectively, against sensitive (MSSA) and resistant strains (MRSA and MDRSA) of S. aureus using a TLC bioautography assay. Erynone (1) exhibited the greatest DPPH free radical scavenging activity. CONCLUSIONS: Seven compounds, including a new chromanone, were isolated from the antimicrobial dichloromethane extract of the stem bark of E. stricta. Six of the seven compounds showed antibacterial and/or antioxidant activities. These findings provide support for the customary (traditional and contemporary) use of E. stricta bark for the treatment of skin and wound infections.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Erythrina/química , Extratos Vegetais/farmacologia , Antibacterianos/química , Antifúngicos/química , Antioxidantes/química , Bactérias/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Estrutura Molecular , Extratos Vegetais/química
16.
Fitoterapia ; 108: 48-54, 2016 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-26592853

RESUMO

Six new flavanones (1-6), together with six known compounds were isolated from Erythrina livingstoniana. Their structures were elucidated on the basis of NMR data and HRMS(n) fragmentation pathway and by comparison with literature data. Compounds 5, 7 and 8 showed remarkable DPPH free radical scavenging efficacies. The compounds, however, did not demonstrate an anti-inflammatory potential when tested using a PGE2 (prostaglandin E2) competitive enzyme immunoassay. The plausible biosynthetic pathways of the isolated compounds are described.


Assuntos
Erythrina/química , Flavanonas/química , Depuradores de Radicais Livres/química , Dinoprostona , Flavanonas/isolamento & purificação , Depuradores de Radicais Livres/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química
17.
Arte Med. Ampl ; 36(4): 152-161, 2016.
Artigo em Português | MOSAICO - Saúde integrativa | ID: biblio-876394

RESUMO

As plantas brasileiras Erythrina mulungu Mart. ex Benth e Erythrina velutina Willd. têm sido utilizadas na medicina popular como sedativas e calmantes naturais para estresse, ansiedade, depressão. São plantas angiospermas, que pertencem à família das leguminosas (Fabaceae/Leguminosae) e subfamília papilionácea (Papilionaceae). Em geral são utilizados extratos das cascas do caule, frutos e folhas da E. velutina e extratos das folhas e flores da E. mulungu. Representam a principal fonte de alcaloides tetracíclicos de atividade similar ao curare, responsáveis por causar paralisia muscular. Resultados de diversos trabalhos mostraram que os alcaloides eritrartina, eritravina, 11-hidroxi-eritravina e os derivados eritrínicos são os principais responsáveis pelo efeito ansiolítico. Através de um levantamento bibliográfico sobre as plantas E. velutina e E. mulungu, no qual as propriedades terapêuticas foram avaliadas em diversos estudos pré-clínicos, observamos atividade ansiolítica com efeitos semelhante aos efeitos dos benzodiazepínicos; atividade sobre o sistema nervoso central com alteração neurotransmissora dos receptores GABA, além de ação anticonvulsivante, sedativa e amnésica; atividade antibacteriana e atividade antinociceptiva. Os aspectos antroposóficos da E. velutina e da E. mulungu apontam para as propriedades da família das leguminosas e da subfamília papilionácea. Sua principal característica é a presença do nitrogênio e o seu princípio astral. As plantas possuem apenas organização física e vital (ou etérica). A ação do anímico (ou astral) ocorre sempre de fora para dentro na planta. Com o surgimento das flores, as plantas se aproximaram do reino animal, entrando em contato com forças astrais que deveriam permanecer no exterior das plantas. Se essa astralidade penetrar na planta, isso se traduz na alteração de forma, de cor, no surgimento de substâncias, como por exemplo, os alcaloides, como tentativa da planta de impedir um processo de "animalização". Portanto, uma planta rica em alcaloides, possui propriedades pertencentes ao reino animal, e quando ingerida por seres humanos, provoca alteração da organização anímica. Assim, as plantas E. velutina e E. mulungu, ricas em alcaloides, promovem paralisia flácida no ser humano, devido à retirada da astralidade da dinâmica neuromuscular, uma vez que esta é responsável pelo tônus muscular e consciência sensorial no organismo. Essa ação deslocadora da organização anímica é responsável pelo efeito ansiolítico e sedativo em casos de distúrbios de ansiedade, estresse, tensão e insônia.(AU)


The Brazilian plants Erythrina mulungu Mart. ex Benth and Erythrina velutina Willd. have been used by the popular medicine as natural sedative and tranquilizing agent for stress, anxiety, depression and insomnia. They are angiosperm plants, which belong to the pea family (Fabaceae/Leguminosae) and the Papilionaceae subfamily. In general, the parts used are stem bark, fruits and leaves (E. velutina), and leaves and inflorescences (E. mulungu). These plants represent the main source of tetracyclic alkaloids and they have curare-like activity, causing muscular paralysis. The result of several studies demonstrated that the alkaloids erythrartin, erythravine, 11-hydroxy-erythravine and the erythrin derivatives are mainly responsible for the anxiolytic effect. After a literature review, in which the therapeutic properties of E. velutina and E. mulungu were analyzed in several preclinical studies, we observed the following: anxiolytic activity with benzodiazepine-like effects; central nervous system activity with alteration of GABA receptors, besides anticonvulsant, sedative and amnesic action; antibacterial activity and antinociceptive activity. The E. velutina and E. mulungu's anthroposophic aspects point to the properties of the pea family and the papilionaceous subfamily. The nitrogen and the astral principle are the main characteristics of these plants. Normally, plants have only physical and vital organization. However, with the flowering process, these plants get closer to the animal kingdom, getting in touch with astral forces that should remain in the external parts of the plants. If the astral forces penetrate into the plant, it will produce poison substances (alkaloids) as an attempt to avoid an "animalization" process. Therefore, an alkaloidrich plant has properties that belong to the animal sphere, and when it is used as medicine by humans, it modifies the soul organization. Thus, E. velutina and E. mulungu, which are rich in alkaloids, cause flaccid paralysis in humans due to the astrality's removal from neuromuscular dynamics, once it is responsible for muscle tone and sensory awareness in the body. This dislocated action of the soul organization is responsible for the anxiolytic and sedative effects in cases of anxiety, stress, tension and insomnia.(AU)


Assuntos
Humanos , Depressão/tratamento farmacológico , Erythrina , Fitoterapia , Preparações de Plantas/uso terapêutico , Antroposofia , Ansiedade/efeitos dos fármacos , Brasil , Erythrina/química
18.
Arte Med. Ampl ; 36(4): 162-167, 2016.
Artigo em Inglês | MOSAICO - Saúde integrativa | ID: biblio-876423

RESUMO

Erythrina é um gênero da família botânica Leguminosae (Fabaceae), que ocorre em todo o território brasileiro. São árvores de porte médio, madeira mole, flores grandes vermelhas ou alaranjadas, que ocorrem numa ampla variedade de habitats, desde matas tropicais até bosques de altitude. Seus frutos e sementes se dispersam pela ação do vento e dos animais. Estão distribuídas majoritariamente nas Américas e na África. No Brasil, são encontradas cerca de 12 espécies de Erythrina, sendo que a espécie E. mulungu Mart. ex Benth (sinonímia: E. verna Vell.) é a mais utilizada para fins medicinais. E. mulungu é uma árvore de 15 a 20 metros de altura, com espinhos ao longo dos troncos, folhas compostas, longamente pecioladas. Perde todas as folhas na época da floração cobrindo-se de inflorescências alaranjadas. Produz pequenos frutos do tipo vagem, de 6 a 12 cm de comprimento, contendo entre uma e três sementes, de cor marrom-clara. Ocorre naturalmente no Cerrado, Amazônia e Mata Atlântica, preferencialmente nas encostas e matas abertas. Tem crescimento rápido, alcançando 3,5 m de altura em dois anos. Preparações de E. mulungu são utilizadas popularmente com o propósito de afastar forças negativas, trazer paz e tranquilidade. É bastante comum a substituição por outras espécies do mesmo gênero, dependendo da disponibilidade local. A ação neurotrópica da planta é explicada pela presença de alcaloides eritrínicos, encontrado principalmente nas sementes e na casca. E. mulungu é mencionada nas principais farmacopeias e compêndios vigentes de fitoterapia e homeopatia, com indicação para quadros leves de ansiedade e insônia. O presente artigo discorre sobre as possibilidades de uso desta planta na medicina antroposófica, de forma isolada, ou em associação com outros insumos farmacêuticos já consagrados.(AU)


Erythrina is a genus of the botanical family Leguminosae (Fabaceae), which occurs throughout the whole Brazilian territory. They are medium-sized trees, with soft wood, big red or orange flowers, which occur in a wide variety of habitats, from the rainforests to the highland woods. Their fruits and seeds are dispersed by wind and animals action. They are distributed mainly in America and Africa. Around 12 species of Erythrina are found in Brazil, of which E. mulungu Mart. ex Benth (synonym: Erythrina verna Vell.) is the therapeutically most used species. E. mulungu is a 15 to 20 m high tree, with thorns along the stems, composed and long-petiolate leaves. It loses all its leaves during the flowering season, when it is covered by orange inflorescences. It bears little bean-type fruits, with 6 to 12 cm long, containing one to three light brown colored seeds. It occurs naturally in the Cerrado, Amazonia and Atlantic Rainforest, preferably at hillsides and open forests. It grows quickly, reaching 3,5 m high in two years. E. mulungu preparations are popularly used to calm down and to remove negative energy. The substitution by other species of the same genus is very common, depending on local availability. The neurotropic action of the plant is explained by the presence of erythrinic alkaloids, found mainly in the seeds and bark. E. mulungu is mentioned in the main current pharmacopeias and compendia of phytotherapy and homeopathy, being indicated for mild anxiety and insomnia. The present article discusses the possibilities of using this plant in anthroposophic medicine, singly or in association to other already established pharmaceutical substances.(AU)


Assuntos
Humanos , Erythrina , Fitoterapia , Preparações de Plantas/uso terapêutico , Distúrbios do Início e da Manutenção do Sono/tratamento farmacológico , Antroposofia , Ansiedade , Brasil , Erythrina/química
19.
Nat Prod Commun ; 11(8): 1099-1102, 2016 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30725567

RESUMO

Utilizing the pER8:GUS transgenic plant bioassay system to monitor estrogenic activity-guided fractionation, one new constituent, erycaffrain A, together with I known compounds were isolated from the ethanolic extract of Erythrina caffra. The structures of the isolated compounds were identified in combination with spectroscopic analyses. This is the first study reporting the estrogenic activity of E. caffra. The new compound exhibited as a SREM, but.also showed both estrogenic and anti-estrogenic activities in the MCF-7 cancer cell model. Several known phytoestrogens in this plant also revealed possible new functions for E. caffra stem.


Assuntos
Erythrina/química , Antagonistas de Estrogênios/química , Estrogênios/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Antagonistas de Estrogênios/farmacologia , Estrogênios/farmacologia , Genes Reporter , Humanos , Células MCF-7 , Estrutura Molecular , Plantas Geneticamente Modificadas
20.
BMC Complement Altern Med ; 15: 453, 2015 Dec 30.
Artigo em Inglês | MEDLINE | ID: mdl-26715029

RESUMO

BACKGROUND: In the present study, the methanol extracts from the leaves, as well as compounds namely sigmoidin I (1), atalantoflavone (2), bidwillon A (3), neocyclomorusin (4), 6α-hydroxyphaseollidin (5) and neobavaisoflavone (6) (from the bark extract) were tested for their activities against a panel of Gram-negative bacteria including multi-drug resistant (MDR) phenotypes. METHODS: Broth microdilution method was used to determine the minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs) of the extracts as well as compounds 1-6. RESULTS: The MIC results indicated that the crude extracts from the leaves and bark of this plant were able to inhibit the growth of 96.3 % of the 27 tested bacteria. Compounds 2-6 displayed selective activities, their inhibitory effects being obtained on 8.3 %, 41.7 %, 58.3 %, 58.3 % and 66.7 % of tested bacteria respectively for 2, 3, 5, 6 and 4. The lowest MIC value of 8 µg/mL was obtained with 6 against Escherichia coli ATCC8739, Enterobacter cloacae ECCI69, Klebsiella pneumoniae KP55, Providencia stuartii NAE16 and Pseudomonas aeruginosa PA01. CONCLUSION: The present study demonstrates that Erythrina sigmoidea is a potential source of antibacterial drugs to fight against MDR bacteria. Neobavaisoflavone (6) is the main antibacterial consituents of the bark crude extract.


Assuntos
Antibacterianos/farmacologia , Farmacorresistência Bacteriana Múltipla/efeitos dos fármacos , Erythrina , Bactérias Gram-Negativas/efeitos dos fármacos , Misturas Complexas/farmacologia , Erythrina/química , Isoflavonas/farmacologia , Testes de Sensibilidade Microbiana , Fenótipo , Casca de Planta , Extratos Vegetais/farmacologia , Folhas de Planta
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